Scott Belsky, Founder, Behance

Scott Belsky: Mastering the Messy Middle

Inspired ideas and triumphant endings occupy every entrepreneur’s imagination, but Behance founder Scott Belsky wants you to focus on the more chaotic part of your creative journey.

Scott Belsky’s rise to success with Behance, a network for creative professionals, happened the way many creative endeavors do—through, as he puts it, “a series of accidents or inspirations.”

But to quote one of his favorite maxims, attributed to Thomas Edison: “Genius is 1 percent inspiration, 99 percent perspiration.” To get to where he is today, Belsky put in a whole lot of sweat equity.

In return, he ended up at the helm of a leading online network and portfolio platform for creative professionals, which sold to Adobe for nine figures in 2012, and hit 10 million members by the end of 2017. Belsky has since taken a top role at Adobe, and become a successful early-stage investor.

Belsky’s still fixated on that journey of bringing ideas into reality, and has a new book all about the “messy middle” stage of creative projects and entrepreneurial ventures.

Humble Beginnings

While Belsky’s passion is empowering creative people, you might not be able to tell from his resume. He studied economics and entrepreneurship as an undergrad at Cornell, went on to receive an MBA from Harvard, and began his career at financial powerhouse Goldman Sachs.

So how did this Ivy League business student and former investment bank employee come to found one of the most influential networks for photographers, designers, illustrators, and more? Like most creatives, Belsky drew upon real life for inspiration. Throughout his early career, he noticed that most ideas never come to fruition, not because the ideas are bad, but because creative people fail to execute them. Often, disorganization plays a huge role.

“I’ve always been obsessed with the idea of helping organize creative people,” he says. And that obsession drove him to launch Behance, a network that enables creative professionals to showcase online portfolios and get discovered more easily.

What most people don’t realize, though, is that Behance started out selling paper products. In 2006, Belsky launched a line of notebooks, cards, and other paper tools to help creatives get organized the old-fashioned way (since taken over by Ghostly). From there, the business evolved into 99U, a conference for creatives. Both of those products were a means to an end: the launch of Behance as a technology platform.

“The paper products and the conference were definitely our bootstrapping mechanism for five years,” he explains. “That was very much a big part of our revenue.”

Though the Behance network launched in 2007, Belsky and his team began working on it in 2005, using no outside funding for those first five years. But as the technology side of it took off, Belsky knew he had to focus his team’s resources. That meant turning away from the paper products and taking on investors in order to rapidly grow the Behance network.

“If you’re going to try a number of different things early on, you also have to be willing to kill a number of things early on,” Belsky says. “That’s the only way you make any one thing succeed.”

Pruning the Bonsai Tree

Writers may be familiar with the concept of “killing your darlings”—removing beloved parts of your story in order to strengthen it overall—but the analogy Belsky uses for business is pruning the Bonsai tree.

“It’s hard to cut those newest little twigs and little leaves,” he explains, “but that’s the art of building a tree and having something that actually has significance and some gravity to it. And I think it’s very much the same thing in a business.”

All that pruning paid off for Belsky. In 2012, Adobe acquired Behance for $150 million, as reported by TechCrunch. From there, Belsky transitioned to Chief Product Officer for Adobe. He’s also an early-stage investor to companies such as Pinterest, Uber, and Warby Parker.

The Messy Middle

To focus only on Belsky’s triumphant exit would be to neglect a stage of the entrepreneurial journey he believes is so important that he wrote an entire book about it: The Messy Middle.

While grandiose beginnings are romantic and victorious endings are gratifying, take a closer look and you’ll see that Belsky labored over Behance for seven years before its acquisition.

“With my story, there was a real, very messy middle,” he explains, “where there was a lot of rebuilding and testing things and getting it wrong and then trying it again and then getting it right—a very volatile journey.”

How volatile? In an interview with Business Insider, Belsky shared some of Behance’s “near-death experiences,” such as the time some ad deals fell through, giving them only one-and-a-half months of runway; the economic downturn of 2008; and the time they had to recode the entire network after realizing they’d built it wrong.

It was close calls such as these that inspired him to write The Messy Middle, in which he teaches founders how to endure the lows, maximize the highs, and not mess it up in the final stretch—something that, as a founder and advisor, he’s seen happen a few times.

“It’s very psychological,” he says. “There’s a few things that happen towards the end of a big project, or you’re right around the opportunity of going public, or an acquisition, or…publishing your book, or sharing your art to the world, or whatever your project is, when you’re on that cusp of success.”

Victory is within reach, and then everything falls apart. What’s at work here? According to Belsky, the first thing is the fear of finishing.

“Makers aren’t used to being done,” he says. “And so the notion…of having a finish of some sort is very disconcerting to many people, even though you’d intuitively think it’s happiness. It’s actually sometimes fear how your life will change, how will people interpret your work, that kind of thing.”

The second factor is self-sabotage, which Belsky has seen happen to many teams when they don’t think they deserve their success.

“There’s a lot of interesting stuff that happens at the end of a journey,” he says. “I just felt like these are things no one ever talks about, and so I try to tackle a little of it at the end of the book.”

So if you’re failing right now, it might not be the end—it might just be your messy middle. Knowing the difference can be difficult, and that’s part of the problem for many entrepreneurs. They give up too soon.

“A big part of successful startups is just sticking together long enough to figure it out,” Belsky says.

So how can you tell whether you should stick it out or shut it down? Belsky offers two guiding principles. First, whenever you add a new feature, think about which one you might take out.

”It sounds a little crazy,” he admits. “But if you are thinking about a new aspect of your product or service and you’re comparing it to another one that you already have live…and you prefer the new one over the old one that’s already live, you should always ask the question ‘Should we just kill the one that’s live?’”

In doing so, you’ll protect the simplicity of your product. And Belsky speaks from experience.

Behance once added a groups product, where users could create groups and have their own exchanges within them. But only about 15 percent of the network actually used it. Meanwhile, the Behance team was devoting a lot of time toward maintaining it. In the end, they decided the groups feature was distracting customers from the core purpose of Behance, building projects and a portfolio. Because of that experience, Belsky recommends the “one feature in, one feature out” principle, even if it’s only in theory.

The second guiding principle in determining whether to give up is reviewing your end goal.

“Yes, it will always get hard and you’ll always lose hope at times,” Belsky says. “But if you look at that end goal, and if you no longer believe that that is the right solution, then you should just start something new. You should give up.”

Busting the Myth of Perfection

Creatives often have reputations for being perfectionists—their work is never “good enough,” never finished. How can creative teams know when it’s the right time to ship the product?

“I think you always have to be shipping,” says Belsky, who cautions against shipping too late and missing the market or shipping too soon and being stuck with a rushed product. The latter is the reason he’s wary of the oft-praised MVP—minimum viable product—that entrepreneurs tout as a way to get started without wasting time and resources.

“There’s all this talk of the MVP,” he says, “and this notion of operating very leanly. However, whatever you start to put in the market for the first time ends up becoming almost like a local maxima of what you can iterate around.”

Admittedly, it’s tough to find that balance. But if you know your customers well and you’ve built your team right, you’ll be able to figure that out together.

“That’s part of the chemistry of a team and having enough empathy with your customers where you can test your product with them and start to get a sense for when you’re offering real value.”

And instead of letting your pursuit of perfection prevent you from ever completing anything, let it drive your desire to create.

“Never be satisfied,” Belsky says. “There’s always something wrong with your product. It’s either not good enough for power users, not good enough for new users, it’s not representative of enough of your goals.”

But it’s by getting that product to market anyway—despite its imperfections—that you’ll learn how it can be better.

3 Tips for Finding Product-Market Fit

Ah, the coveted “product-market fit,” defined by investor Marc Andreessen as “being in a good market with a product that can satisfy that market.”

Quiz any founder on that term and they’ll probably know it well, but the question of how to get there still haunts them. Belsky offers this advice:

Be driven by empathy for your customers, not passion for your solution.

“People get very motivated by what they think they need to create that their customers want versus seeking additional empathy with the people suffering the problem, which means to constantly be with your customers. And before you get product-market fit, that’s what it is all about.”

Step away from the computer.

“We make mistakes when we stay behind our computer screens and try to innovate within our own team a solution that may in fact not be practical. And so I think that’s part of it is to keep seeking more and more, keep peeling the onion and getting to this core of the truth of what is really…the pain point you’re trying to solve.”

Stick together long enough.

“So few teams actually stay together long enough to iterate and try new things. And I think one of the most important things we had at Behance was our culture. It was just a team that was passionate about the customer base and loved working together, and we just stuck together long enough that suddenly stuff started to gel.”

Building a Team and Creating a Culture

According to Belsky, one of the most important things Behance had was its culture. So how can founders create a culture that attracts and retains the right people?

“A culture is nothing but the stories that you share,” Belsky says. “So one thing you have to do is make sure you create the stories and then you share the stories. Creating the stories literally means investing time with the team together, having experiences together, chronicling what people go through, the funny things that happen, the realizations, the principles that emerge, and where they came from.”

If you want those stories to continually shape the culture, you must retell them to each new member of the team.

“That’s a big part of being the steward of a culture,” he says. “Another thing is recognizing that every new member of your team changes the DNA of the culture.”

If that’s true, then it’s worth being picky about whom you choose to add to your team. When it comes to new hires, Belsky favors those who take initiative, and have a history of doing so, over those who have experience.

“I think you find, in the early stages, that those who are those initiators—the ones who will just, whatever it is that they’re tasked on, they’ll just go above and beyond—typically overperform versus those who just have a deep expertise.”

When you’re starting out, Belsky says it helps to have generalists on your team so you can tackle any of the myriad of problems that could come your way in the beginning.

“That needs to be the expectation of anyone who joins the team in the early stages,” he says.

But once you start to develop your business and hire, for example, your first backend engineer or your first data scientist, it’s time to bring in the specialists.

“The decisions that those people make impact the future of your company,” he says. “So those are areas where you want to have someone who’s a specialist.”

And so everyone can do their best work, take a page from Behance’s book and consider implementing a liberal culture for feedback exchange—including debriefs after every major project or launch—to promote open communication and foster improvement.

“It was a really important way for us to just reflect and appreciate those who contributed to the success,” he says of that practice. “And then also just critique ourselves.”

Embrace Your Own Messy Middle

With The Messy Middle slated for release in October 2018, Belsky is excited to bring this multi-year project to fruition and get more than 100 insights into the hands of entrepreneurs everywhere who are navigating their own messy middles. While he doesn’t like to prescribe rigid rules, he hopes readers will consider the book’s ideas, challenge them, and see what works for their own journeys.

But most of all, Belsky hopes that entrepreneurs stick with it—whatever that labor of love may be.

“I just have this routine realization with so many different teams I work with,” he says, “that when they just stick together long enough, and they just keep getting closer and closer to a problem they’re trying to solve for their customer…a labor of love has a way of working out, just not as you expect.”

If we can learn anything from Belsky’s career, it’s that, sometimes, things turn out far better than anyone could have expected.

Key Takeaways

Two guiding principles on whether to stick it out or shut it down

Why Belsky is wary of the MVP craze, and how to balance perfectionism with action

Three tips for finding true product-market fit

How to create a startup culture that attracts and retains the right people

Why Belsky started Behance and what inspired his progress

Full Transcript of Podcast with Scott Belsky

Nathan: So the first question that I ask everyone that I speak to is, how did you get your job?

Scott: Oh, yeah. I think that like most careers, it’s sort of … it’s always a series of or inspirations. And for me, I’ve always been obsessed with the idea of helping organise creative people, and that materialised into the idea of Behance, which actually most folks don’t realise started as a paper company and then for organising creative people. So we actually built notebooks and that kind of thing to help creatives get organised. And that evolved into a conference that was dedicated to organisation in the creative world, and talking about ideas, and talking about how to actually make them happen, which led to a book called, “Making Ideas Happen,” which was also in parallel to building a platform called Behance to help creatives organise their work, and get attribution, and opportunity.

And then when you build a few different strands of a concept, you never really know which one’s gonna stick. And in our case, a few of them actually are still around today. Our conference is in it’s 11th year. Those paper products are still marketed. But, Behance is really what we’re known for and that business has been a decade of my labour. Of course, Behance led to me coming into Adobe and then taking on a new role I have now, which is leading all of the products for the company.

Nathan: Yeah, wow. So that’s really fascinating. Curious, so you started … where did … take me back. When did you start … so it sounds like 99U was kind of … and the physical products, that was kind of the first kind of … was that your first venture?

Scott: Yeah, that’s when it all started. And I think that the … it was just out of my own frustration with myself and with other creative people I knew who always had ideas, and talked about them, but never actually got anything done because we were always overwhelmed by our day jobs and also the long-term pursuit. It was really hard to stay engaged with.

One of the things I talk about a lot with startup teams is we’re all sort of hardwired with a short-term reward system. We work for this salary, we work for the gratification of customers who are working with us, or clients, or our bosses, or that sort of thing. And then when you commit yourself to an entrepreneurial pursuit, you’re unplugging yourself from this reward system motivated only by a long-term vision, something you want to accomplish through a lot of work. And that works for the first few weeks, maybe, but eventually you realise, “Wow, actually the long-term vision is not enough to keep me and my team engaged for years.” You actually have to have short-term rewards as well, and that often comes in the form of early products you can actually get to market while you’re building your real products, or other hacks of the reward system, other ways of staying engaged. And for us at Behance, it was some of these early things that we did, like the paper products and the conference, were actually what helped us stay engaged long enough to build the company that we ended up being known for, which was more the technology.

But, you asked kind of back to the early days and what the impetus of those products was. It was really just a genuine interest in the problem.

Nathan: Yeah, I see. So did you start … you said Behance spun off from the conference, though. So you building another tech product before that? And it sounds like your using the paper products and the conference to cash flow you guys?

Scott: Yeah, well the paper products and the conference were definitely our bootstrapping mechanism for five years. That was very much a big part of our revenue. Behance was the first technology product that we had, or real service. We also had a product called Action Method, which some folks might remember. But it was a task management tool for creatives that was more inspired by the paper product line. But, we ended up killing that, which is another big lesson by the way that I’ll just jump to real quick. Which is the fact that you have to … if you’re gonna try a number of different things early on, you also have to be willing to kill a number of things early on. That’s the only way you make any one thing succeed.

Nathan: Yeah, because focus is so key.

Scott: Focus is key. And the analogy I like to use it’s like a Bonsai tree where you’re always kind of cutting back the branches, the old branches, in order … or the new branches, in order to make the real branches bigger. And it’s hard to cut those new little twigs, and little leaves, and stuff, but that’s the art of building a tree and actually having something that actually has significance and some gravity to it. And I think its very much the same thing in the business, certainly in entrepreneurship, and also the same thing for writers. In writing, they call it killing your darlings. The plot points or the character that you fall in love with as a writer but aren’t necessarily central to the audience and will ultimately confuse people.

Nathan: So take me back just on the … so I can kind of get a gauge for the timeline, and our audience can get a gauge for the timeline. Because you look at Behance, you sold … it was acquired by Adobe in 2012. So that was six years ago. So this has been a decent period of time. So when … and you said that you didn’t get to Behance until five years after starting the company. So when did you guys start, and how long did it take to really keep fit with the Behance platform?

Scott: Well, Behance we started working on in 2005. And really over 2006 we launched the paper products. And then, in 2007, we launched the network. But, if you think about it, from 2005 to 2012, that was seven years, five years of bootstrapping, and two years of by the company.

Nathan: Yeah, wow. And how come you guys decided to raise after five years? Because that’s kind of uncommon, right?

Scott: I think it’s actually more uncommon to wait that long. We really had this desire to build a business that we could self-fund, in some ways the old-fashioned way, hand to mouth. And also, by doing that we could have our to build it at the pace we wanted to and to do the projects that we wanted to do in the order we wanted to do them. So, that’s the only way to control your own destiny, in some cases, is to actually be in control and be funding yourself.

But, at some point we realised that part of the business, the technology side, was growing very rapidly and we needed to resource the teams appropriately. And when I had teams come to me saying, “Hey, I don’t feel like I can do the best work of my life here unless I can hire the team that I need,” I realised that it was time to get some investors, so we could grow a little faster.

Nathan: So, the space in between when you launched Behance and then actually it went on to be acquired, it’s a decent amount of time. But, what I’m curious around is, you said you were working on the product … you launched in 2005, but didn’t launch until five years later, so when you were building it, was it what you guys had mentioned? Or were there many pivots along the way?

Scott: Well, we started … in 2005, and the paper products came out 2006, and the network launched 2007. So are you asking what we did during those two years or what we did between that and the acquisition?

Nathan: What did you do between that and the acquisition?

Scott: Oh, well I mean I was building a company. So between the launch in 2007 and 2012, we built a team of 35, 40 people that were dedicated exclusively to the Behance network side of our business. We had to build many incarnations of Behance. We’re always improving it, and adding new dimensions to it, and cutting certain dimensions to it, and getting more feedback, and building the business side in terms of the sales for the many lines of revenue we’ve tested over the years of Behance as we’ve built our business. So that was the core business and product building phase of Behance before the acquisition.

Nathan: So the reason I ask that question is I wanted to talk to you about your latest book, “The Messy Middle,” finding your way through the hardest and most crucial part of any bold venture. Can you talk to us, or elaborate, why did you decide to write this book and what would you like to share with our audience to give us a bit of a teaser of what they can expect, and everything you’ve learned? Because not only have you built an incredible platform, like I said offline before we hit record … we use Behance to find exceptional design talent. We’re bootstrapped, and we can find exceptional design talent all around the world. A lot of Foundr side and all the collateral we put out, it’s all due to your platform, which is incredible.

But, you’re also an early stage investor and active advisor to companies, exceptional companies with true worth and significance like Uber, Warby Parker, Pinterest, Periscope. So I’m just really curious. Talk to us about your new book. It’s coming out soon.

Scott: Sure. Obviously with my story, there was a real very messy middle where there was a lot of rebuilding, and testing things, and getting it wrong, and then trying again, and then getting it right; a very volatile journey. And what I have subsequently learned by being an investor and advisor to many of the companies you mentioned, and others, that are still very much in their messy middle is just how common that is, and how much volatility there is, and how much of the journey boils down to just two things. How you endure the lows, and how you optimise the highs. How you endure the anonymity, the ambiguity, the uncertainty, that lack of that short-term reward system I mentioned earlier, and how you optimise the parts of your product that get attention, the ways that you work that seem to be effective.

And I just realised that was the rhythm of making that I observed some of the best entrepreneurs and creative leaders operate around. And so I started to chronicle them, and this started actually five or six years ago, writing down these insights that I would hear, whether it was in board meetings, or people I observed, or my own experiences. And The Messy Middle is my attempt to package it up and share it.

So there’s three parts in the book. There’s endurance, there’s optimization, as I mentioned, and there’s a small part at the end called, “The Final Mile,” which is about how we make sure we don’t mess it all up right before we’re done something. Which I’ve also seen happen a few different times.

And so it’s meant to be a manual for that extraordinarily volatile journey and I couldn’t be more excited to get it into the hands of people that are embarking on their own creative journeys and building things.

Nathan: Yeah, amazing. I can’t wait to get a copy and have a read. Can you give us some examples? What I find interesting is you said people, perhaps towards the end, perhaps getting close to acquisition or something, you said are messing things up. Can you give us some examples or insights you’ve chronicled there?

Scott: Well, I think that it’s very psychological. I think that there’s a few thing that happen towards the end of a big project, or right around the opportunity of going public, or an acquisition, or publishing your book, or sharing your art to the world, or whatever your project is. When you’re on that cusp of success to something, or completion, first of all, makers aren’t used to being done. And so the notion of having a finish of some sort is very concerting to many people even though you would intuitively think it’s happiness, it’s actually sometimes fear. How your life will change, how will people interpret your work, that kind of thing.

I think there’s also an element of self-sabotage that sometimes happens for many people who don’t feel they deserve their success. I’ve seen people on teams, whether they’ve been my team or others, where they just couldn’t internalise the thought that they deserve it. And as a result, they start doing things that in some ways sabotage their own success.

So there’s a lot of interesting stuff that happens at the end of a journey and I just felt like these are things no one ever talks about. And so I try to tackle a little of it at the end of the book.

Nathan: And when it comes to a creative project, when do you know when to shift as a creative? Because like you said, does perfect exist?

Scott: Well, I think you always have to be shipping. I’ve seen some teams wait too long to ship and they kind of miss their market. I’ve seen another concept I’ve been a little critical of in my experience is in shipping too soon. There’s all this talk of the MVP, the minimal viable product, and this notion of operating very leanly. However, whatever you start to put in market for the first time, ends up becoming almost like a local maxima of what you can iterate throughout. And so I think when teams ship too early, and get something out there too early, sometimes they feel stops iterating what they’ve shipped so quickly versus getting the real, core, right product before sharing it with the world.

Nathan: So how do you know? How do you find that balance?

Scott: I think that’s part of the chemistry of a team, and having enough empathy with your customers where you can test your product with them, and start to get a sense for when you’re offering real value. What I always like to … my trick in that sort of decision, is I always challenge teams to optimise for the problems that they want to have. So for example, if you launch a product and your customers want to pay you for this additional feature, or they want to … they’re asking you, “Oh my God, this is so useful. I want to be able to store this other type of data in it,” or “I want to be able to do this other thing.” That’s the kind of stuff you want to have as requests from your customers. And so those are things you want to optimise for adding and you should ship your products before those features are in there so you can then have the customers request those things later.

What you don’t want to do is ship your product before customers even know what the heck it is, and how to use it, or why it’s valuable. So you wanna make sure that there’s some core value that gets people engaged, but you don’t want to ship so late that you’re not getting that of requests coming in for things that they want now that they love your product so much.

Nathan: And around your creative, sounds like by the heart, what are your thoughts on perfection? Does it exist?

Scott: Well, the pursuit of perfection certainly exists even though perfection doesn’t. And I think that kind of drives down to that principal I have as someone who builds products for a living, digital products in my case, is to never be satisfied. I mean, there’s always something wrong with your product. It’s either not good enough for power users, not good enough for new users, it’s not representative enough of your goals, and every time you get it into market you learn how it can be better, and you wanna change it, and eventually it will be disrupted, unless you disrupt yourself by doing something that replaces your product. So I think perpetual dissatisfaction, it is important, which essentially means that perfection doesn’t exist.

Nathan: You talk about the product, and you’re a product guy. I think, undeniably, one thing that is going to make your startup work is if you have an exceptional product that is far superior to what anything else out there in the marketplace. I think that’s gotta fundamentally be the goal with whatever market you’re looking to disrupt, or whatever product you’re building. What advice would you give to our audience and founders that are on their journey to just starting to build out their MVP? On their journey, I guess perhaps, found product market fit. What are your thoughts there?

Scott: I think a few things. First of all, make sure you’re being driven by empathy with your customers over the passion you have for the solution. That’s a common mistake is that people get very motivated by what they think they need to create that their customers want versus seeking additional empathy with the people suffering the problem. Which means to constantly be with your customers and before you get product market fit, that’s what it is all about. And we make mistakes when we stay behind our computer screens and try to innovate within our own team a solution that may, in fact, not be practical. And so I think that’s part of it is to keep seeking more and more … keep peeling the onion, getting to the core of the truth of what is really the pain point you’re trying to solve.

I think also a big part of successful startups is just sticking together long enough to figure it out. So few teams actually stay together long enough to iterate, and try new things. And I think one of the most important things we had at Behance was our culture. It was just a team that was passionate about the customer base, and loved working together, and we just stuck together long enough that suddenly stuff started to gel.

Nathan: Yeah, that’s really interesting. Can you tell me about that early culture and what advice you would give to founders that are building their founding team around how to foster a great culture.

Scott: A culture is nothing but a story that you share that end up setting the tone and setting the chemistry of the team. And so one thing you have to do is make sure you create the stories, and then you share the stories. Creating the stories literally means investing time with the team together, having experiences together, chronicling what people go through, the funny things that happen, the realisations, the principles that emerge and where they came from. And then you retell those stories to every new member of the team. That’s a big part of being the steward of the culture.

Another new thing is recognising that every new member of your team changes the DNA of the culture, and you have to always adjust and reset when each person joins. And I always try to do that. I always try to make sure every new member of our team felt as a founder of some part of the team. Because in truth, when you’re starting a company, everyone is doing something for the first time. And in that sense, everyone is a founder of one part of the business.

Nathan: And when it comes to founding teams, do you prefer when you’re building them out, specialists or all-rounders? How do you like to approach that in the early days?

Scott: I think that there are some areas … it always helps to have some generalists on the team in the early stages who can just tackle any problem, and just kind of roll up their sleeves. I think that needs to be the expectation of anyone who joins the team in the early stages. However, I also think that certainly when you start to balance certain parts of your, whether it be your first back end engineer, or your first front end engineer, or your first data scientist, obviously the decisions that those people make impact the future of your company. So those are areas where you wanna have someone who’s a specialist.

Nathan: And when it comes to building teams, do you have any rules that you’d like to share? Or any golden, “It’s gotta be this way,” from your experience?

Scott: Well, in the new book, in The Messy Middle, I do talk a lot about optimising a team, what that really boils down to. Whether it’s simple things, like the things you don’t get cheap on, like things like space and computer screens, and stuff like that for your team that are essential. To practises for exchanging feedback, and for making sure that the team is committed to not only doing the work, but optimising how they work. And also about hiring and initiative, people who take initiative in things, and having a history of doing so, versus experience. I think you find in the early stages that those who are those initiators, the ones who are just … whatever it is that they’re tasked on, they’ll just go above and beyond, typically over perform. Versus those who just have a deep expertise.

So there’s a lot of practises I think you have to consider as you build the dream team. And it depends, though. I mean, every company is different, every culture is different. I try not to prescribe any sort of rule, but rather prompt founders, and leaders with the right insight so they can kind of craft their own play book.

Nathan: And at Behance, how did you encourage and ensure that your team did their best work? How did you facilitate and foster that?

Scott: We had a liberal culture for feedback exchange. We would always do debriefs after every major project or launch. And that was a really important way for us to and appreciate those who contributed to the success, and then also just critique ourselves. What could’ve been better? Almost always there was a communication issue where one team would say to the other team, “Listen, I don’t feel like you gave me enough heads up on that,” or feel like we had enough time for this, or we didn’t plan appropriately. And that’s just building the muscle memory of our team of how we can operate better. And I think that’s best practise to do that.

Nathan: Wanna switch gears just coming back to … you talked about, even with your journey as a founder where you started with the conference and the physical product that you ended up cutting that to focus on the network, and you referred to a Bonsai tree. I’m curious. How do you know when to give up? How do you know what to drop? How do you know what to focus on? How do you work that out? Because I think that is often a difficult thing to wrestle with as a founder because you talk about grit, but then at the same time there’s a lot of … people wanna do it all. It’s shiny object syndrome. So many things going on. We’ve talked about team building, we’ve talked about culture, we’ve talked about product, we’ve talked about a little bit of finance, versus bootstrapping. It’s just so much going on. It’s a battlefield. How do you know when to give up? When to keep going? How to cut?

Scott: I think there’s two principles that I think are helpful. I think one is, whenever you add a new feature, consider which one you might take out. It sounds a little crazy, but if you are thinking about a new aspect of your product or service, and you’re comparing it to another one that you already have live, and you prefer the new one over the old one that’s already live, you should always have the question, “Should we just kill the one that’s live as we add this new thing?” This is how you keep simplicity in a product, and it can also be a forcing function for a team to say, “Hey, that thing that we launched” …

For us, one of them was groups. We had this groups product in Behance were people could create groups and have their own exchanges. And it was used by 15% of the network. So we spent a lot of time always catering to it. And it also, I think, distracted customers from what was really central in Behance. It was about building your project, and building your portfolio, keeping it updated. And so one thing you can do is sort of like one feature in, one feature out. Or at least have a practise where you consider doing it.

And I think the other thing is if you’re doing something, and you don’t love it, if you could go back you wouldn’t start the business to begin with, then stop. I always tell teams, “You’re not stuck.” It doesn’t matter if you raise capital or whatever. If you don’t believe in the premise, if you’re not … yes, it will always get hard, and you’ll always lose hope at times, but if you look at that end goal and you no longer believe that that is the right solution, then you should just start something new. You should give up.

Nathan: That’s great advice. Thank you. We have to work towards wrapping up, but I think our audience would love to know just around your investor and advisor side as a founder, how did you come to be involved in also picking such amazing startups that you’re involved in? Like Air Bnb, Pinterest, Uber. Can you talk to us about that?

Scott: Sure. I wish I was an investor to Airbnb. I’m not, to be clear. For the others you mentioned, I am. These are all other founders that were product-centric, and in the early days when they were trying to get a small group of seed investors, you could also be value add in other ways by helping products. I decided to invest as a support, as an investor as well. And that’s always been my approach as a seed investor is to find teams that I believe in, products that I really resonate with and can stay up late at night thinking about. I call it the zen of a product. If I can really zero into what the zen of the product is, what is it’s purpose in the world, then I feel like I can add some value to this, and if they’re raising a seed round I’ll participate. So that’s always been my … a lot of other criteria as well, of course. But, that’s sort of my my role as an investor.

Nathan: Yeah, the zen of the product. I find that quite interesting. So, we have to work towards wrapping up because I know we’re taking up a bit of your time now. But, I guess the last piece of the puzzle is where can people find out more about your latest book, The Messy Middle, and any kind of parting words you’d like to finish off with?

Scott: Yeah, sure. Well, listen, The Messy Middle has really been a five to seven year project for me. There are over 100 insights in there that are all about optimising, and enduring through the messy middle of a bold entrepreneurial pursuit or creative journey. I just encourage people to let them play in their heads a little bit, roll around, challenge them in your mind just to start to figure out what works for you and what doesn’t. But, I’m really excited to get it into folks’ hands. And of course The Messy Middle will be available October 2nd everywhere, and it’s available for pre-order now.

And I think as parting words of wisdom, I just think that … I don’t know. I hope that people go do And whether it’s one idea, or an idea that you decide is a better idea. But I just have this routine realisation with so many different teams I work with that when they just stick together long enough, and they just keep getting closer, and closer to a problem they’re trying to solve for their customer, I think typically a labour of love has a way of working out, just not as you expect. And so I hope everyone tries to find that, and never gives up on the discipline of becoming a better maker, building that muscle memory through your own experiences, and through insights that others share with you.

Nathan: Amazing. Well look, thank you so much for your time, Scott. You’ve been very, very generous and shared so much gold with our audience. I really, really appreciate the time you’ve taken and congratulations on all your success thus far.